The Corner Office Archives

The Leader’s Toolkit: Questions That Unlock Truth in One-on-Ones

“Tell me one thing you really like about the organization, and one thing that frustrates you about the company?”

“Tell me what you do here, that’s not in your job description, that you think is really critical?”

“Tell me something you think I don’t know, that you think I should know, that is important?”

These questions come from The Corner Office, a former New York Times column by Adam Bryant, where he interviewed CEOs about how they lead. They remain as apt today as ever for senior executives looking to spark honest conversations in one-on-one interactions.

Other leadership thinkers have expanded this questioning approach. In Reinventing Leadership, Robert Townsend and Warren Bennis, and in The Hard Thing About Hard Things, Ben Horowitz, recommend CEOs ask questions such as:

Your first meeting, as a leader of a new team, is crucial

“(Bryant) What were some early moves you made, in terms of culture, in your current role?

(Kenny) From Day 1, I wanted to establish that it was a culture of respect and generosity and truthfulness, and that we were going to work together to solve problems.

On my first day, I met all the employees at a quarterly ad sales meeting The first presentation started – and this was January 2012 – and we had just come off a big quarter because of Hurricane Irene.

Adam Bryant CEO David Kenny First impressions New York Times PowerPoint The Corner Office The Weather Company